반응 #7072

반응 방정식

Triethylene glycol monomethyl ether

triethylamine

cyclopropanecarbonyl chloride

→

title product

Cyclopropanecarboxylic Acid, 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl Ester

용매

dichloromethane

반응 조건

후처리

1. 1
   온도maintaining the temperature at 0° C. with constant stirring
2. 2
   기타quenched with saturated ammonium chloride solution
3. 3
   기타It was then transferred to a separatory funnel
4. 4
   세척washed with 5% sodium bicarbonate (2×5 ml), 1:1 hydrochloric acid (2×5 ml)
5. 5
   기타The dichloromethane layer was separated from the aqueous layer
6. 6
   건조dried over anhydrous sodium sulphate
7. 7
   여과filtered
8. 8
   기타evaporated in vacuo

실험 절차

Triethylene glycol monomethyl ether (1.1 eq, 5.26 mmol, 0.84 ml), triethylamine (1.1 eq, 5.26 mmol, 0.73 ml) was taken in a 10 ml round bottom flask and dichloromethane (3 ml) was added. This mixture was cooled to 0° C. and then cyclopropanecarbonyl chloride (4.78 mmol, 0.5 g, 0.43 ml) was added in a dropwise fashion maintaining the temperature at 0° C. with constant stirring. A yellowish-orange solid was observed after some time. Stirring was continued for 1 hr at 0° C. The reaction was monitored by thin layer chromatography, and then quenched with saturated ammonium chloride solution. It was then transferred to a separatory funnel, washed with 5% sodium bicarbonate (2×5 ml), 1:1 hydrochloric acid (2×5 ml) and then with brine (5 ml). The dichloromethane layer was separated from the aqueous layer, dried over anhydrous sodium sulphate, filtered, and evaporated in vacuo to give the title product as a pale yellow liquid. Purification was attempted by flash chromatography and vacuum distillation (b.p.=144° C., 3.0 mm of Hg) which afforded the pure product as a colorless liquid (527.0 mg, 48%).

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